#------------------------------------------------------------------------------
#$Date: 2019-12-26 22:22:08 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/19/2311935.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2311935
loop_
_publ_author_name
'Brisdon, Alan K.'
'Muneer, Abeer M. T.'
'Pritchard, Robin G.'
_publ_section_title
;
 Halogen bonding in a series of Br(CF₂)ₙBr-DABCO
 adducts (n = 4, 6, 8).
;
_journal_coeditor_code           UK3139
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              874
_journal_page_last               879
_journal_paper_doi               10.1107/S2053229617013663
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C4 Br2 F8, C6 H12 N2'
_chemical_formula_moiety         'C4 Br2 F8, C6 H12 N2'
_chemical_formula_sum            'C10 H12 Br2 F8 N2'
_chemical_formula_weight         472.04
_chemical_name_systematic
;
1,4-Dibromoperfluorobutane--1,4-diazabicyclo[2.2.2]octane (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.271(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4659(6)
_cell_length_b                   11.0854(6)
_cell_length_c                   10.7955(6)
_cell_measurement_reflns_used    1842
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      27.3000
_cell_measurement_theta_min      3.6490
_cell_volume                     1546.95(14)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector_area_resol_mean 8.0714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6191
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         3.386
_exptl_absorpt_coefficient_mu    5.320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.027
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.515
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0076P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0554
_refine_ls_wR_factor_ref         0.0644
_reflns_number_gt                2260
_reflns_number_total             3034
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            uk3139sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1546.96(15)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2311935
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Br Br1 0.47057(3) 0.36072(4) 0.13908(5) 0.02488(13) Uani d 1
Br Br2 -0.07338(3) 0.33779(4) -0.18506(5) 0.02532(13) Uani d 1
C C1 0.3492(3) 0.3537(4) -0.0077(5) 0.0282(12) Uani d 1
C C2 0.2501(3) 0.3426(4) 0.0330(4) 0.0202(10) Uani d 1
C C3 0.1478(3) 0.3489(4) -0.0796(5) 0.0208(10) Uani d 1
C C4 0.0488(3) 0.3080(4) -0.0446(5) 0.0240(11) Uani d 1
F F1 0.35763(18) 0.2579(3) -0.0792(3) 0.0613(10) Uani d 1
F F2 0.34425(18) 0.4521(3) -0.0793(3) 0.0598(10) Uani d 1
F F3 0.25256(16) 0.2386(2) 0.0954(3) 0.0434(8) Uani d 1
F F4 0.24725(17) 0.4318(2) 0.1146(3) 0.0456(8) Uani d 1
F F5 0.15754(17) 0.2775(2) -0.1749(3) 0.0408(8) Uani d 1
F F6 0.13500(16) 0.4625(2) -0.1215(3) 0.0398(8) Uani d 1
F F7 0.05584(16) 0.1913(2) -0.0158(3) 0.0429(8) Uani d 1
F F8 0.04251(17) 0.3683(2) 0.0599(3) 0.0387(7) Uani d 1
C C5 0.6632(3) 0.2423(4) 0.4059(5) 0.0264(11) Uani d 1
H H5A 0.6997 0.1996 0.3510 0.032 Uiso calc 1
H H5B 0.5974 0.1996 0.3992 0.032 Uiso calc 1
C C6 0.5907(3) 0.4310(4) 0.4455(4) 0.0297(12) Uani d 1
H H6A 0.5239 0.3917 0.4415 0.036 Uiso calc 1
H H6B 0.5764 0.5153 0.4154 0.036 Uiso calc 1
C C7 0.7404(3) 0.4287(4) 0.3691(4) 0.0255(11) Uani d 1
H H7A 0.7268 0.5133 0.3400 0.031 Uiso calc 1
H H7B 0.7763 0.3881 0.3122 0.031 Uiso calc 1
C C8 0.7308(3) 0.2414(4) 0.5477(5) 0.0291(12) Uani d 1
H H8A 0.6929 0.2007 0.6023 0.035 Uiso calc 1
H H8B 0.7950 0.1953 0.5541 0.035 Uiso calc 1
C C9 0.6604(3) 0.4305(4) 0.5864(5) 0.0317(12) Uani d 1
H H9A 0.6763 0.5145 0.6166 0.038 Uiso calc 1
H H9B 0.6233 0.3912 0.6428 0.038 Uiso calc 1
C C10 0.8092(3) 0.4258(4) 0.5097(5) 0.0309(12) Uani d 1
H H10A 0.8745 0.3831 0.5132 0.037 Uiso calc 1
H H10B 0.8266 0.5094 0.5403 0.037 Uiso calc 1
N N1 0.6416(2) 0.3667(3) 0.3606(3) 0.0222(9) Uani d 1
N N2 0.7574(2) 0.3650(3) 0.5949(4) 0.0219(9) Uani d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 Br1 112.0(3)
F1 C1 Br1 108.5(3)
F1 C1 C2 109.0(3)
F2 C1 Br1 109.7(3)
F2 C1 C2 109.2(3)
F2 C1 F1 108.4(4)
C1 C2 C3 115.2(4)
F3 C2 C1 108.4(3)
F3 C2 C3 108.9(3)
F3 C2 F4 108.0(4)
F4 C2 C1 108.7(3)
F4 C2 C3 107.4(3)
C4 C3 C2 115.4(4)
F5 C3 C2 108.5(3)
F5 C3 C4 107.0(3)
F6 C3 C2 107.9(3)
F6 C3 C4 108.7(3)
F6 C3 F5 109.3(4)
C3 C4 Br2 111.2(3)
F7 C4 Br2 109.9(3)
F7 C4 C3 109.4(3)
F7 C4 F8 107.9(4)
F8 C4 Br2 109.7(3)
F8 C4 C3 108.8(3)
H5A C5 H5B 108.2
C8 C5 H5A 109.6
C8 C5 H5B 109.6
N1 C5 H5A 109.6
N1 C5 H5B 109.6
N1 C5 C8 110.1(3)
H6A C6 H6B 108.1
C9 C6 H6A 109.5
C9 C6 H6B 109.5
N1 C6 H6A 109.5
N1 C6 H6B 109.5
N1 C6 C9 110.5(3)
H7A C7 H7B 108.2
C10 C7 H7A 109.8
C10 C7 H7B 109.8
N1 C7 H7A 109.8
N1 C7 H7B 109.8
N1 C7 C10 109.5(3)
C5 C8 H8A 109.5
C5 C8 H8B 109.5
H8A C8 H8B 108.1
N2 C8 C5 110.8(3)
N2 C8 H8A 109.5
N2 C8 H8B 109.5
C6 C9 H9A 109.6
C6 C9 H9B 109.6
H9A C9 H9B 108.1
N2 C9 C6 110.2(4)
N2 C9 H9A 109.6
N2 C9 H9B 109.6
C7 C10 H10A 109.3
C7 C10 H10B 109.3
H10A C10 H10B 108.0
N2 C10 C7 111.6(3)
N2 C10 H10A 109.3
N2 C10 H10B 109.3
C5 N1 C6 109.4(3)
C5 N1 C7 109.0(3)
C6 N1 C7 107.7(3)
C8 N2 C9 108.1(3)
C10 N2 C8 108.8(3)
C10 N2 C9 107.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 1.933(4) y
Br2 C4 1.928(4) y
C1 C2 1.523(5) y
C1 F1 1.336(5) y
C1 F2 1.328(5) y
C2 C3 1.562(5) y
C2 F3 1.331(4) y
C2 F4 1.333(4) y
C3 C4 1.551(5) y
C3 F5 1.334(5) y
C3 F6 1.333(4) y
C4 F7 1.328(4) y
C4 F8 1.334(5) y
C5 H5A 0.9900 ?
C5 H5B 0.9900 ?
C5 C8 1.546(6) y
C5 N1 1.465(5) y
C6 H6A 0.9900 ?
C6 H6B 0.9900 ?
C6 C9 1.547(6) y
C6 N1 1.472(5) y
C7 H7A 0.9900 ?
C7 H7B 0.9900 ?
C7 C10 1.541(6) y
C7 N1 1.477(4) y
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
C8 N2 1.471(5) y
C9 H9A 0.9900 ?
C9 H9B 0.9900 ?
C9 N2 1.475(4) y
C10 H10A 0.9900 ?
C10 H10B 0.9900 ?
C10 N2 1.465(5) y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
Br1 C1 C2 C3 174.3(3)
Br1 C1 C2 F3 -63.4(4)
Br1 C1 C2 F4 53.8(4)
C1 C2 C3 C4 166.2(4)
C1 C2 C3 F5 46.2(5)
C1 C2 C3 F6 -72.1(4)
C2 C3 C4 Br2 173.3(3)
C2 C3 C4 F7 -65.2(5)
C2 C3 C4 F8 52.4(5)
F1 C1 C2 C3 -65.6(5)
F1 C1 C2 F3 56.7(5)
F1 C1 C2 F4 173.9(4)
F2 C1 C2 C3 52.6(5)
F2 C1 C2 F3 174.9(4)
F2 C1 C2 F4 -67.9(5)
F3 C2 C3 C4 44.2(5)
F3 C2 C3 F5 -75.8(4)
F3 C2 C3 F6 165.9(3)
F4 C2 C3 C4 -72.6(4)
F4 C2 C3 F5 167.4(3)
F4 C2 C3 F6 49.1(4)
F5 C3 C4 Br2 -65.9(4)
F5 C3 C4 F7 55.6(5)
F5 C3 C4 F8 173.2(3)
F6 C3 C4 Br2 51.9(4)
F6 C3 C4 F7 173.4(4)
F6 C3 C4 F8 -69.0(5)
C5 C8 N2 C9 60.2(4)
C5 C8 N2 C10 -56.5(4)
C6 C9 N2 C8 -58.5(5)
C6 C9 N2 C10 59.0(4)
C7 C10 N2 C8 58.4(4)
C7 C10 N2 C9 -58.6(4)
C8 C5 N1 C6 -57.3(4)
C8 C5 N1 C7 60.3(4)
C9 C6 N1 C5 58.8(4)
C9 C6 N1 C7 -59.5(4)
C10 C7 N1 C5 -58.5(4)
C10 C7 N1 C6 60.0(4)
N1 C5 C8 N2 -2.2(5)
N1 C6 C9 N2 -0.3(5)
N1 C7 C10 N2 -1.0(5)
